# US 5,703,084 A · Adenosine deaminase inhibitors

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- Number: US 5,703,084 A
- Document ID: US5703084A
- Status: Granted
- Kind: A
- Application number: 08/680,413
- Filed: 1996-07-15
- Granted: 1997-12-30
- Earliest claimed: 1996-07-15
- Assignees: The Board of Governors for Higher Education, State of Rhode Island and Providence Plantations
- Inventors: Elie Abushanab; Palle V. P. Pragnacharyulu
- Web page: https://patentgrep.com/patent/US5703084A

## CPC

- C07D 473/00: Heterocyclic compounds containing purine ring systems
- A61P 43/00: Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- A61P: SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS

## Abstract

This invention disclosed (2S,3R)-3(6-aminopurin-9-yl) aralkan-2-ols, a novel class of adenine derivatives (also called 9-aralkyladenines, ARADS), which have been shown to inhibit the enzyme adenosine deaminase at therapeutically useful levels. The relevant inhibitory constant (K.sub.i) values are in the range of 10.sup.-7 -10.sup.-10 M. These compounds with potencies in this range can reversibly inhibit ADA in an effective manner, without permanently deactivating the enzyme. ADA inhibitors that have similar biological profiles have been shown to be of therapeutic value when used to protect heart muscle against ischemic damage.

## Claims

### Claim 1

A compound of: ##STR2## where n=0-4 and R is selected from the group consisting of 4--CH.sub.3 ; 3--CH.sub.2 CH.sub.3 ; 2--CH.sub.2 CH.sub.2 CH.sub.3 ; H; 3--CH.sub.3 ; 2--CH.sub.2 CH.sub.3 ; ›H! 2--CH.sub.3.

### Claim 2 (depends on 1)

The compound of claim 1 wherein n=0, R=4--CH.sub.3.

### Claim 3 (depends on 1)

The compound of claim 1 wherein n=0, R=3--CH.sub.2 CH.sub.3.

### Claim 4 (depends on 1)

The compound of claim 1 wherein n=0, R=2--CH.sub.2 CH.sub.2 CH.sub.3.

### Claim 5 (depends on 1)

The compound of claim 1 wherein n=1, R=H.

### Claim 6 (depends on 1)

The compound of claim 1 wherein n=1, R=3--CH.sub.3.

### Claim 7 (depends on 1)

The compound of claim 1 wherein n=1, R=2--CH.sub.2 CH.sub.3.

### Claim 8 (depends on 1)

The compound of claim 1 wherein n=2, R=H.

### Claim 9 (depends on 1)

The compound of claim 1 wherein n=2, R=2--CH.sub.3.

### Claim 10 (depends on 1)

The compound of claim 1 wherein n=3, R=H.

### Claim 11 (depends on 1)

The compound of claim 1 wherein n=4, R=H.

### Claim 12 (depends on 1)

A composition comprising a compound of claim 1; or
a pharmacologically acceptable salt thereof; or
a pharmacologically acceptable isomer thereof which inhibit adenosine deaminase activity with a Ki value between about 10.sup.-7 and about 10.sup.-10 ; or
a combination of the same.